27 Windward St, Mashpee, MA 02649
Property image
Property image
OFF MARKET

$556,700

Trulia Estimate
  • 2 Beds
  • 2.5 Baths
  • 2,000 sqft

27 Windward St, Mashpee, MA 02649

Est. Refi. Payment $3,185/mo*
Refinance Your Home
Currently Off Market - Sold Feb 28, 2022 for $494,000

Home Value

Trulia Estimate
$557K
Since last month
Increased$400 (+0.1%)
Since last year
Decreased$26K (-4.4%)
Since last sale
Increased$62K (+12.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
August 2026$556K
July 2026$556K
June 2026$558K
May 2026$565K
April 2026$566K
March 2026$565K
February 2026$560K
January 2026$557K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
80 Pine Hill Blvd #80, Mashpee, MA
0.00
Condo
$520,000
07/30/26
2
2.5
2,208
12 Kettle Ln #31, Mashpee, MA
0.00
Condo
$475,000
06/22/26
2
2
1,606
5 Kettle Lane #38, Mashpee, MA
0.00
Condo
$575,000
03/12/26
2
3
2,342
17 Chadwick Court, Mashpee, MA
0.00
Condo
$556,000
01/07/26
2
2
2,325
106 Pine Hill Blvd, Mashpee, MA
0.00
Condo
$485,000
06/23/26
2
2
1,338
1 Par 3 Court UNIT 1, Mashpee, MA
0.00
Condo
$675,000
05/06/26
2
3
2,338
2 Pacific Ave #2, Mashpee, MA
0.00
Condo
$543,000
09/18/25
2
2
1,421
2 Pacific Avenue, Mashpee, MA
0.00
Condo
$543,000
09/18/25
2
2
1,421
50 Pine Hill Blvd #46, Mashpee, MA
0.00
Condo
$474,000
04/08/26
2
2
1,338
72 Pine Hill Boulevard UNIT 72, Mashpee, MA
0.00
Condo
$465,000
05/08/26
2
2
1,338

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3 Kettle Lane, Mashpee, MA 02649
0.00
$527,300
2
2.5
1,685
Off Market
1 Upland Circle, Mashpee, MA 02649
0.00
$459,000
2
2
1,333
Recently Sold
19 Executive Drive, Mashpee, MA 02649
0.00
-
2
2.5
1,829
Off Market
19 Bonwood Drive, Mashpee, MA 02649
0.00
$511,500
2
2
1,338
Off Market
2 Pga Lane, Mashpee, MA 02649
0.00
$535,000
2
2.5
1,685
Recently Sold
25 Grey Hawk Drive, Mashpee, MA 02649
0.00
$651,800
2
2
1,596
Off Market
17 Chadwick Court, Mashpee, MA 02649
0.00
$556,000
2
2
2,325
Recently Sold
70 Grey Hawk Drive, Mashpee, MA 02649
0.00
$654,800
2
2
2,032
Off Market
6 Chadwick Court, Mashpee, MA 02649
0.00
$639,000
2
2
1,862
For Sale
5 Woods Edge Lane UNIT 5, Mashpee, MA 02649
0.00
$527,500
2
2
1,333
Recently Sold
15 Classic Circle UNIT 15, Mashpee, MA 02649
0.00
$499,900
2
2
1,333
For Sale
10 Kettle Lane, Mashpee, MA 02649
0.00
$515,000
2
2.5
1,686
Recently Sold

Local Information

  • Map ViewExplore the area around 27 Windward St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
2000
Living Area
2,000 sqft
Price/Sqft
$278
Parking
Garage

About this House

Southport, Cape Cods premiere 55 community with its award-winning resort lifestyle is perfect for the active adult and a dream retirement! The unsurpassed amenities and activities include a 9-hole golf course clubhouse, 32,000 sq ft Village center, indoor/outdoor pools, tennis, pickleball, billiard room, spas, gyms, grand ballroom, library, workshops, travel clubs, leagues social groups. This popular Provincetown duplex model allows for easy one floor living with a private driveway. Its fantastic floor plan offers an open layout with good light exposure, cozy but elegant fireplaced living/dining room, vaulted ceiling, gleaming hardwood floors, dry bar, and access to a good size back deck. The galley kitchen has light and bright white cabinetry and granite countertops. Down the hall you will find a guest bedroom/den, a full tiled bath, handy first floor laundry and direct access to the garage. The spacious Master suite has a large walk-in closet and private bath. Lastly, the beautifully finished 10-year young lower level provides lots of additional space for visiting friends, family and entertaining with its additional half bath, custom cedar closet, and loads of storage.
27 Windward St, Mashpee, MA 02649 is a 2 bedroom, 3 bathroom, 2,000 sqft condo built in 2000. It last sold for $494,000 on Feb 28, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $556,700, with a rent estimate of $3,412/month.

Home Details for 27 Windward St

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2000Year Updated: 2000
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Feb 28, 2022
Source: N/A
Sold
$494,000
Jan 15, 2022
Source: CCIMLS #22200166
Pending
$489,000
Jan 13, 2022
Source: CCIMLS #22200166
Listed For Sale
$489,000
Sep 8, 2008
Source: CCIMLS #20707641
Sold
$297,000
Apr 9, 2001
Source: N/A
Sold
$212,900

Market trends in Mashpee

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$666K
$1.17KMoM
Sale-to-List Price
98.6%
0.2%MoM
Price per sq ft
$405
$7MoM
Available listings
135
3MoM

Around this home

What Locals Say about Mashpee

At least 83 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say it's dog friendly

  • 84 % Say parking is easy

  • 80 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 77 % Say it's quiet

  • 73 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 64 % Say people would walk alone at night

  • 61 % Say neighbors are friendly

  • 55 % Say kids play outside

  • 40 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say there are sidewalks

  • 24 % Say it's walkable to grocery stores

  • 19 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Tyler Williams
    "We visit frequently and it’s always a pleasure to get away from the city. The “cape air” always has the food & drink taste better "
    0
    Flag
  • Shirleyrief
    "With easy access to Rt 28, commuters will find both bridges just 15 minutes away. Summer commutes are easy. Take a half day on Friday to arrive and a half day for a Monday morning return."
    5
    Flag
  • Tabetha L.
    "my neighborhood is quiet and has lots of families. i feel safe to let me kids go out and play without supervision cause we all watch each others kids"
    1
    Flag
  • Cordom33
    "Fireworks on the docks are a really good time. There are actually two public docks that are fun with family. "
    0
    Flag
  • Mauramurray
    "Nice neighborhood. Feels safe. Many say school system is excellent. Mashpee commons is a tremendous asset"
    6
    Flag
  • Brigitte A.
    "I am not aware of any community events. much of the year people are not here. I've lived here for 4 years and do not know any of my neighbors. no one has ever introduced themselves to me."
    0
    Flag
  • Trulia User
    "very quiet but friendly area, neighborhood. many people use their mashpee house as their summer home, but will mostly come on summer weekends. So it is very quiet."
    0
    Flag
  • Tonkahyde
    "I have lived here since 1986, my sons grew up here. Great school system but Town Hall leaves a lot to be desired.New sidewalks will improve pedestrian safety.Reasonable tax rate."
    4
    Flag
  • Rickferrari223
    "Community Center July 4 children’s baseball and races . They also have teenage dances in the summer"
    0
    Flag
  • Pmbrennan
    "This is a quiet street and we know each other. We have children playing and riding bikes in the street in the summer. The neighborhood has half year round residence and half permanent residence. "
    5
    Flag
  • Pmbrennan
    "Great street with friendly neighbors and close proximity to shopping, golf, and the beach. Also, close to Bourne and Sagamore bridges! "
    2
    Flag
  • Pmbrennan
    "I walk my dog in the morning and night. Everyone is friendly and clean up after their dogs. I see several people on my walks and there is never a problem. It is safe and enjoyable! "
    6
    Flag
  • Florence S.
    "Quiet. Great for young families. We know most people in town. Beaches are wonderful and the trails in our backyard go on for miles and miles. "
    5
    Flag
  • Blackheartz
    "It takes me minutes to get to work , stores, gas, liquor store & great restaurants, close to highway to get the Cape."
    0
    Flag
  • erinbanner
    "I've lived in this community for 3 years. The town is small enough to know and take care of each other and yet big enough to bring businesses and new opportunities for all ages. "
    2
    Flag
  • Johan B.
    "Oktoberfest, seaside lemans. barnstable fair , scallopfest. Falmouth road race. best buddies race. "
    0
    Flag
  • Atputdy1
    "Great walking areas ..... low car traffic .... friendly neighbors ..... close to willowbend golf course "
    1
    Flag
  • Jodi L. J.
    "I have lived here for over 20 years an enjoy the amount of space and community around. It is a quiet friendly neighborhood."
    3
    Flag
  • Pegala22
    "Pot lucks at the community house for those who are here year round. There is a full summer schedule of events including a 5k, earth day clean up and art events to name a few. "
    0
    Flag
  • Nancy S.
    "Beautiful area. 1 mile from Mashpee Commons, 4 miles from the beach. "
    0
    Flag
  • Ellen K.
    "I live here all year round and just love the lake, which Massachusetts' hidden treasure. If you love your privacy - yet want to have access to loads of activities - Mashpee-Wakeby Lake is the place for you!! It is Paradise on earth!!"
    0
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  • Deb B.
    "I grew up on Mashpee-Wakeby Lake in the summers and now live here full-time. It is total paradise all year long. I love the lake and waking up in the morning to it and see the trees through my skylights. I love to hear the birds singing and see the swans on the lake. It is heaven. And there is so much to do in the area - there is Mashpee Commons and South Cape Village, with their shops and restaurants, and the local library that has just been built - gorgeous - and theaters and movie houses. Plus, Mashpee is only one hour from Boston, so if you want even more excitement or want to commute for your work, you can get home to your paradise so easily."
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 27 Windward St

  • What is 27 Windward St estimated to be worth?
    Trulia's estimated value for 27 Windward St in Mashpee, MA is $556,700.
  • What is the price history for 27 Windward St?
    27 Windward St in Mashpee, MA last sold for $494,000 in February 2022.
  • Is Mashpee a buyer's or seller's market?
    Mashpee is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Mashpee?
    The median sale price in Mashpee is $666K. That is down $1.17K from the prior month.

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